Merck
All Photos(2)

295817

Sigma-Aldrich

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene

97%

Synonym(s):
(R)-(+)-BINAP, (R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine)
Linear Formula:
[(C6H5)2PC10H6-]2
CAS Number:
Molecular Weight:
622.67
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

solid

optical activity

[α]19/D +233°, c = 0.3 in toluene

optical purity

ee: 99% (HPLC)

mp

239-241 °C (lit.)

SMILES string

c1ccc(cc1)P(c2ccccc2)c3ccc4ccccc4c3-c5c(ccc6ccccc56)P(c7ccccc7)c8ccccc8

InChI

1S/C44H32P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-32H

InChI key

MUALRAIOVNYAIW-UHFFFAOYSA-N

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General description

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.

Application

Useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation and disilylation. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.
Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes. Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds.

Packaging

250 mg in glass insert
1, 5 g in glass bottle

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Sci. Synth., 1, 113-264 (2002)
Tetrahedron, 50, 335-335 (1994)
Masanori Kawasaki et al.
Journal of the American Chemical Society, 128(51), 16482-16483 (2006-12-21)
This communication describes studies in which an azo hetero-Diels-Alder adduct was furnished in high regio- and enantioselectivity using azopyridine as a reagent and silver as a catalyst. The obtained hetero-Diels-Alder adduct was easily converted to the corresponding chiral 1,4-diamino alcohol.
Journal of Organometallic Chemistry, 692, 550-550 (2007)
2,2'-bis (diphenylphosphino)-1, 1'-binaphthyl (binap): A new atropisomeric bis (triaryl) phosphine. synthesis and its use in the Rh (l)-catalyzed asymmetric hydrogenation of a-(acylamino) acrylic acids.
Miyashita A, et al.
Tetrahedron, 40(8), 1245-1253 (1984)

Articles

BINAP/SEGPHOS® Ligands and Complexes

We present an article concerning BINAP/SEGPHOS® Ligands and Complexes.

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